Sodium hydride → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2-methyl-1-(1-methylethyl)propyl]imidazole-5-carbonitrile

HRID 52938Notes

Reaction equation

HRID 52938 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([C:18]#[N:19])=[C:8]([C:10]([OH:17])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])[N:9]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:29]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:24][CH:23]=1.[H-].[Na+]>CN(C)C(=O)C>[C:37]([O:36][C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:6]2[C:7]([C:18]#[N:19])=[C:8]([C:10]([OH:17])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:12])[CH3:13])[N:9]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:23][CH:24]=1)=[O:35])([CH3:40])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178441741HCID 178441741, compound

Product 1

HCID 190361471-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-(1-hydroxy-2-methyl-1-(1-methylethyl)propyl]imidazole-5-carbonitrileYield 90.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 45(a), but using 282 mg of 2-butyl-4-[1-hydroxy-2-methyl-1-(1-methylethyl)propyl]imidazole-5-carbonitrile (prepared as described in Preparation 30), 409 mg of t-butyl 4'-(bromomethyl)biphenyl-2-carboxylate and 47 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) in 5 ml of N,N-dimethylacetamide, 513 mg of the title compound were obtained as a viscous oil.

Sources & evidence

ORD record
ord-43f8f20380c04e6d989c3ad72739c366
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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